2-Nitroanisole → Ethyl 2-(3-methoxy-4-nitrophenyl)propanoate

Temperature

-30 °C

To a stirred solution of 1-methoxy-2-nitrobenzene (3 g, 19.59 mmol) in dimethylformamide were added potassium tert-butoxide (8.792 g, 78.36 mmol) and ethyl 2-chloropropionate (2.5 ml, 19.59 mmol) while maintaining temperature below −30° C. The reaction mixture was stirred for 5 min at −30° C., then ethyl 2-chloropropionate (0.25 mL, 1.959 mmol) was added to mixture. The reaction mixture was stirred for 10 min at room temperature. The residue was dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. Ethyl 2-(3-methoxy-4-nitrophenyl)propanoate (683 mg) was obtained as 14% yield.

1. temperaturewhile maintaining temperature below −30° C
2. stirringThe reaction mixture was stirred for 10 min at room temperature
3. washwashed with water and brine
4. dry with materialThe organic layer was dried over magnesium sulfate
5. filtrationfiltered
6. customThe filtrate removed in vacuo
7. customThe crude was purified by column chromatography

ORD record

ord-8d1c8e7d90004f6481305c9d37ff316e

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08937092B2